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Fangming Liu - One of the best experts on this subject based on the ideXlab platform.
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synthesis and structure characterization of 1 5 Benzothiazepine derivatives bearing quinoline moiety
ChemInform, 2016Co-Authors: Y M Zeng, H H Zeng, Fangming LiuAbstract:A series of 1,5-Benzothiazepine derivatives bearing quinoline moiety were obtained by 1,5-Benzothiazepine containing 2-phensulfanyl-quinoline (4a, 4b, 4c) with equimolar amounts of benzohydroximinoyl chlorides 5 in CH2Cl2 at room temperature. Structures of new compounds were confirmed by elemental analysis, IR, 1H-NMR, MS, and X-ray diffraction analysis.
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design and synthesis of novel 2 1 2 4 triazol 1 yl quinoline based tricyclic 1 5 Benzothiazepine derivatives
ChemInform, 2016Co-Authors: Le Huang, Tinghong Fei, Fangming LiuAbstract:A series of new tricyclic 1,5-Benzothiazepine derivatives containing 2-(1,2,4-triazol-1-yl)quinoline were synthesized by the reaction of 1,5-Benzothiazepine with benzohydroximinoyl chlorides via 1,3-dipolar cycloaddition reaction. The structures of the target compounds were confirmed by IR, 1H NMR, MS, elemental, and X-ray crystallographic analysis.
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synthesis and structure characterization of new 1 2 4 triazolo 5 4 d 1 5 Benzothiazepine derivatives through 1 3 dipolar cycloaddition reaction
ChemInform, 2011Co-Authors: Fangming Liu, Yinglei ZhouAbstract:Novel heterocycles (III) are obtained regioselectively by 1,3-dipolar cycloaddition of in situ generated nitrilimines to Benzothiazepines (I).
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synthesis of 1 5 Benzothiazepine derivatives bearing 2 phenoxy quinoline moiety via 1 3 diplolar cycloaddition reaction
Molecular Diversity, 2011Co-Authors: Zhiqiang Dong, Fangming Liu, Zailiang YuanAbstract:A series of 1,5-Benzothiazepine derivatives were synthesized by the reaction of 1,5-Benzothiazepine containing 2-phenoxy-quinoline with benzohydroximinoyl chlorides and hydrazonoyl chlorides at room temperature. The structures of these novel compounds were confirmed by spectrum, elemental, and X-ray crystallographic analysis.
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synthesis and structure characterization of new 1 2 4 triazolo 5 4 d 1 5 Benzothiazepine derivatives through 1 3 dipolar cycloaddition reaction
Journal of Heterocyclic Chemistry, 2011Co-Authors: Fangming Liu, Yinglei ZhouAbstract:Reaction of 1,5-Benzothiazepines 3, obtained from chalcones 2 and o-aminobenzenthiol, with the (phenylhydrazino) chloromethylenecarboxylates 4 in the presence of Et3N leads to a series of new [1,2,4]triazolo[5,4-d][1,5]Benzothiazepine derivatives 5. Their structures were established using spectroscopic methods and that of compound 5d was confirmed using X-ray diffraction analysis. J. Heterocyclic Chem., (2011).
Yinglei Zhou - One of the best experts on this subject based on the ideXlab platform.
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synthesis and structure characterization of new 1 2 4 triazolo 5 4 d 1 5 Benzothiazepine derivatives through 1 3 dipolar cycloaddition reaction
ChemInform, 2011Co-Authors: Fangming Liu, Yinglei ZhouAbstract:Novel heterocycles (III) are obtained regioselectively by 1,3-dipolar cycloaddition of in situ generated nitrilimines to Benzothiazepines (I).
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synthesis and structure characterization of new 1 2 4 triazolo 5 4 d 1 5 Benzothiazepine derivatives through 1 3 dipolar cycloaddition reaction
Journal of Heterocyclic Chemistry, 2011Co-Authors: Fangming Liu, Yinglei ZhouAbstract:Reaction of 1,5-Benzothiazepines 3, obtained from chalcones 2 and o-aminobenzenthiol, with the (phenylhydrazino) chloromethylenecarboxylates 4 in the presence of Et3N leads to a series of new [1,2,4]triazolo[5,4-d][1,5]Benzothiazepine derivatives 5. Their structures were established using spectroscopic methods and that of compound 5d was confirmed using X-ray diffraction analysis. J. Heterocyclic Chem., (2011).
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synthesis and structure characterization of new 1 2 4 oxadiazolo 4 5 d 1 5 Benzothiazepines derivatives containing 2 phenyl 1 2 3 triazole through 1 3 dipolar cycloaddition reaction
Molecular Diversity, 2008Co-Authors: Debao Yang, Fangming Liu, Chun Yang, Songwei Shen, Yinglei ZhouAbstract:Reaction of 1,5-Benzothiazepines, containing 2-phenyl-1,2,3-triazole 2a–d, with aryl nitrile oxides in CH2 Cl2 at room temperature leads to a series of novel 1,2,4-oxadiazolo[4,5-d]-1,5-Benzothiazepine derivatives 3a-l in good yields. The products were characterized by IR, 1H NMR, MS, elemental analyses, X-ray and their spectrum characters were discussed.
X U Jiaxi - One of the best experts on this subject based on the ideXlab platform.
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differentiation of constitutional isomer of 2 2a 3 4 tetrahydro 4 methyl 2a phenyl 2 thiophen 2 yl 1h azeto 2 1 d 1 5 benzothiazepin 1 one 5 oxide and fragmentations of 2 3 dihydro 2 4 diphenyl 1 5 Benzothiazepine 1 oxide 1 1 dioxide
高等学校化学研究(英文版), 2005Co-Authors: X U JiaxiAbstract:Mass spectrometric behaviour of 2,2a,3,4-tetrahydro-4-methyl-2a-phenyl-2-(thiophen-2-yl)-1H-azeto[2,1-d][1,5]benzothiazepin-1-one-5-oxide and 2,3-dihydro-2,4-diphenyl-1,5-Benzothiazepine-1-oxide/-1,1-dioxide have been studied with the aid of mass-analyzed ion kinetic energy spectrometry and accurate mass measurements under electron impact ionization. The monooxide derivatives showed a tendency to eliminate an alkene or an oxygen atom. 1H-Azeto[2,1-d][1,5]benzothiazepin-1-one-5-oxide could also eliminate the thiophen-2-ylketene molecule via a reverse [2+2] cycloaddition. 2,3-Dihydro-2,4-diphenyl-1,5-Benzothiazepine-1-oxide/-1,1-dioxide could eliminate SO_2 or SO, respectively. The structure of 2,2a,3,4-tetrahydro-4-methyl-2a-phenyl-2-(thiophen-2-yl)-1H-azeto[2,1-d][1,5]benzothiazepin-1-one-5-oxide was identified on the basis of its fragmentation. The identification was supported by the fragmentations of model compound, 2,3-dihydro-2,4-diphenyl-1,5-Benzothiazepine-1-oxide/-1,1-dioxide.
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A structurally diverse heterocyclic library: A Benzothiazepine-fused beta-lactam library derived from reaction of 2,3-dihydro-1,5-Benzothiazepines and acyl chlorides: Synthesis and stereochemistry
molecular diversity, 2005Co-Authors: X U JiaxiAbstract:A 1H-azeto[2,1-d][1,5]benzothiazepin-1-one, beta-lactam derivatives of dihydroBenzothiazepines library derived from reactions of 2,4-disubstituted 2,3-dihydro-1,5-Benzothiazepines and acyl chlorides, including phthalimidoacetyl chloride, chloroacetyl chloride, dichloroacetyl chloride and phenoxyacetyl chloride, was built up through parallel solution-phase synthesis. Stereochemistry of 1H-azeto[2,1-d][1,5]benzothiazepin-1-ones in the reaction process is discussed.Biochemistry & Molecular BiologyChemistry, AppliedChemistry, MedicinalChemistry, MultidisciplinarySCI(E)PubMed9ARTICLE1-345-49
Luca Bernardi - One of the best experts on this subject based on the ideXlab platform.
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organocatalytic asymmetric sulfa michael addition of 2 aminothiophenols to chalcones first enantioselective access to 2 3 4 5 tetrahydro 1 5 Benzothiazepines
European Journal of Organic Chemistry, 2017Co-Authors: Vasco Corti, Patricia Camarero Gonzalez, Julie Febvay, Lorenzo Caruana, Andrea Mazzanti, Mariafrancesca Fochi, Luca BernardiAbstract:1,5-Benzothiazepine frameworks are highly relevant in medicinal chemistry. Reported catalytic asymmetric approaches to these scaffolds have targeted 2,3-dihydro-1,5-benzothiazepin-4-ones, leaving the corresponding amines (2,3,4,5-tetrahydro-1,5-benzo-thiazepines) out of reach. Herein, we present the first entry to these important compounds in enantioenriched form. Our approach is based on the catalytic asymmetric sulfa-Michael addition of 2-aminothiophenols to trans-chalcones, followed by intramolecular reductive amination. Both reactions have required a careful study to solve several challenging issues. The resulting optimized two-step protocol afforded a range of 2,3,4,5-tetrahydro-1,5-Benzothiazepines as single trans-diastereoisomers in moderate to good yields and enantioselectivities.
Pál Sohár - One of the best experts on this subject based on the ideXlab platform.
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novel indole syntheses by ring transformation of β lactam condensed 1 3 benzothiazines into indolo 2 3 b 1 4 Benzothiazepines and indolo 3 2 c isoquinolines
Tetrahedron, 2012Co-Authors: Peter Csomos, Antal Csámpai, L Fodor, Pál SohárAbstract:Abstract ortho-Nitrophenyl-substituted condensed 1,3-benzothiazines proved to be a useful core unit in indole syntheses under non-reductive conditions. Thus, the treatment of ortho-nitro-2-aryl-2a-chloro-4H-azeto[2,1-b][1,3]benzothiazin-1-ones with sodium methoxide in methanol provided indolo-1,4-Benzothiazepines via a novel rearrangement. Through the sulfur extrusion reaction of indolo[2,3-b][1,4]Benzothiazepines, further alkaloid-type indole derivatives, indolo[3,2-c]isoquinolines, were obtained. The structures of the new ring systems were determined by means of NMR spectroscopy.
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expected and unexpected reactions of 1 3 benzothiazine derivatives i ring transformation of β lactam condensed 1 3 benzothiazines into 4 5 dihydro 1 4 Benzothiazepines and indolo 1 4 Benzothiazepines
Tetrahedron Letters, 2011Co-Authors: L Fodor, Peter Csomos, Antal Csámpai, Tamas Holczbauer, Alajos Kalman, Pál SohárAbstract:Abstract The ring-enlargement reactions of monochloro-β-lactam-fused 2-aryl-1,3-benzothiazines revealed that the reactions of ortho-nitro aryl-substituted derivatives with sodium methoxide in methanol provided two products, depending on the amount of the base. With 2 equiv of reagent, the expected 1,4-Benzothiazepines were obtained. Somewhat surprisingly, treatment with a large excess of sodium methoxide led to the formation of indolo-1,4-Benzothiazepines via a novel rearrangement. The structures of the new ring systems were determined by means of X-ray crystallography and NMR spectroscopy.
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A Convenient Synthesis of 1,4-Benzothiazepinesfrom 1,3-Benzothiazines via the Ring Transformation of β-Lactam-Condensed1,3-Benzothiazine Derivatives
Synthesis, 2010Co-Authors: Lajos Fodor, Peter Csomos, Antal Csámpai, Pál SohárAbstract:A convenient synthesis was devised for rare 2,3-disubstituted 4,5-dihydro-1,4-Benzothiazepines from 2-aryl-4H-1,3-benzothiazines. The Staudinger reaction of 1,3-benzothiazines obtained with chloroacetyl chloride selectively furnished trans-monochloroβ-lactam-condensed thiazines. The ring expansion of azeto[2,1-b][1,3]benzothiazin-1-one derivatives with sodium methoxide afforded 1,4-Benzothiazepines as the sole product in good yields. The structures of the new molecules were proved by means NMR and IR spectroscopy.
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exceptional isolation of both imine and enamine desmotropes of 4 1 Benzothiazepines
Tetrahedron, 2010Co-Authors: Peter Csomos, Antal Csámpai, Pál Sohár, L FodorAbstract:Abstract The desmotropy of differently substituted (R∗)-3-ethoxycarbonyl-2-aryl-3,5-dihydro-4,1-Benzothiazepines and 3-ethoxycarbonyl-2-aryl-1,5-dihydro-4,1-Benzothiazepines was investigated. The target 4,1-Benzothiazepines were obtained via the ring transformation of (2R∗,2aS∗)-2-chloro-2a-aryl-2,2a-dihydro-2H,4H-azeto[1,2-a][3,1]benzothiazin-1-ones with sodium ethoxide in ethanol. The β-amino ester intermediate of the ring-enlargement reaction was isolated. Surprisingly, the desmotropes obtained could be separated by column chromatography and proved to be unexpectedly stable in solution. Further comparative studies revealed the existence of only the enamine forms of regioisomeric 2-ethoxycarbonyl-3-aryl-4,5-dihydro-7,8-dimethoxy-1,4-Benzothiazepine derivatives; in this case, no desmotropy occurred. The structures were proved by means of NMR and IR spectroscopy.